I refrained from wearing a pocket square on the first date with my current girlfriend, my roommates said it was "too much". Later on I asked her if I had worn it on the first date if she would have gone on subsequent dates with me, she replied jokingly "possibly not" but then added that it would have been a little weird for a first date but not deal breaker.

Now she gives me unsolicited advice and critique on my pocket square combinations and folds (usually pretty good advice tough). One time I didn't wear a pocket square to a party and she immediately asked me why I was missing one!

I refrained from wearing a pocket square on the first date with my current girlfriend, my roommates said it was "too much". Later on I asked her if I had worn it on the first date if she would have gone on subsequent dates with me, she replied jokingly "possibly not" but then added that it would have been a little weird for a first date but not deal breaker.

Now she gives me unsolicited advice and critique on my pocket square combinations and folds (usually pretty good advice tough). One time I didn't wear a pocket square to a party and she immediately asked me why I was missing one!

If I were going out in jeans and a sport coat, I would skip it. The OP implied he'd already be wearing a suit so I think the PS is appropriate.

What is the intent of this date? In other words, does she know that you are legitimately interested in her, or is there ANY chance at all she thinks this is just a "lunch between friends/coworkers?" Because there's a big difference Pocket square will only help in the latter case. Otherwise it's a distraction imo.

Good questions. She doesn't know there's legitimate interest, but there's an inkling. I'm going for the impression that I've given it some thought, but not *too* much thought, if you get my drift. Going to a cafe/wine bar, nice decor but nothing overly flash. May just try to nail the shirt/tie combo. Dark charcoal suit with light blue pinstripe, white with fine light blue check shirt, and baby pink paisley tie. Thoughts - any better colours for ties? Thanks for all the ideas, chaps.

OP, if a little piece of fabric sticking out of your pocket makes it or breaks with a woman, then you don't want anything to do with her anyway. Just wear what you want to wear and don't worry about it.

1. DO NOT pay for her lunch
2. Ensure that within five minutes of sitting down she knows this isn't casual lunch between friends, i.e. you are interested in more than her accounting skills.
3. Pocket square can work in this case but it should be the last thing on your mind, so if you aren't 100% comfortable wearing it, leave it at the desk.

easy there tiger. If you're attached in any way, do you do exactly as your woman tells you? Me either. I was simply offering once again, POV. Not what my w0menz commands me to do. but spanx for noticing. =)